CS226013B2 - Method of preparing di-ammonium salt of 7beta-(d-(carboxy(4-hydroxyphenyl)-acetyle-amino)-7alpha-methoxy-3-(l(1-methyl-1h-tetrazol-5-yl)-thio)methyl)-8-oxo-5-oxa-1-azabicyclo(4,2,0)oct-2-ene-2-carbaoxylic acid - Google Patents
Method of preparing di-ammonium salt of 7beta-(d-(carboxy(4-hydroxyphenyl)-acetyle-amino)-7alpha-methoxy-3-(l(1-methyl-1h-tetrazol-5-yl)-thio)methyl)-8-oxo-5-oxa-1-azabicyclo(4,2,0)oct-2-ene-2-carbaoxylic acid Download PDFInfo
- Publication number
- CS226013B2 CS226013B2 CS803045A CS304580A CS226013B2 CS 226013 B2 CS226013 B2 CS 226013B2 CS 803045 A CS803045 A CS 803045A CS 304580 A CS304580 A CS 304580A CS 226013 B2 CS226013 B2 CS 226013B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- salt
- solution
- methyl
- epimer
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- 239000002253 acid Substances 0.000 title claims description 10
- -1 1-methyl-1h-tetrazol-5-yl Chemical group 0.000 title abstract 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 48
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 32
- 239000000243 solution Substances 0.000 claims description 27
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 10
- 239000000908 ammonium hydroxide Substances 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 3
- SCNWTQPZTZMXBG-UHFFFAOYSA-N 2-methyloct-2-enoic acid Chemical compound CCCCCC=C(C)C(O)=O SCNWTQPZTZMXBG-UHFFFAOYSA-N 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000003782 beta lactam antibiotic agent Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000002132 β-lactam antibiotic Substances 0.000 abstract 1
- 229940124586 β-lactam antibiotics Drugs 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 230000003115 biocidal effect Effects 0.000 description 4
- 238000006345 epimerization reaction Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- JWAPDSXGXBNOQU-UHFFFAOYSA-N azane;oct-1-ene Chemical compound N.CCCCCCC=C JWAPDSXGXBNOQU-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/035,037 US4252953A (en) | 1979-05-01 | 1979-05-01 | Antibiotic crystalline epimer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS226013B2 true CS226013B2 (en) | 1984-03-19 |
Family
ID=21880235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS803045A CS226013B2 (en) | 1979-05-01 | 1980-04-30 | Method of preparing di-ammonium salt of 7beta-(d-(carboxy(4-hydroxyphenyl)-acetyle-amino)-7alpha-methoxy-3-(l(1-methyl-1h-tetrazol-5-yl)-thio)methyl)-8-oxo-5-oxa-1-azabicyclo(4,2,0)oct-2-ene-2-carbaoxylic acid |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US4252953A (ro) |
| EP (1) | EP0018811B1 (ro) |
| JP (1) | JPS55153788A (ro) |
| KR (1) | KR840000078B1 (ro) |
| AR (1) | AR230450A1 (ro) |
| AT (1) | AT370108B (ro) |
| AU (1) | AU538283B2 (ro) |
| BE (1) | BE882980A (ro) |
| BG (1) | BG34905A3 (ro) |
| CA (1) | CA1138867A (ro) |
| CH (1) | CH646434A5 (ro) |
| CS (1) | CS226013B2 (ro) |
| DD (1) | DD150352A5 (ro) |
| DE (1) | DE3061751D1 (ro) |
| DK (1) | DK177980A (ro) |
| EG (1) | EG14719A (ro) |
| ES (1) | ES8105316A1 (ro) |
| FI (1) | FI801345A7 (ro) |
| FR (1) | FR2455605A1 (ro) |
| GB (1) | GB2047707B (ro) |
| GR (1) | GR68202B (ro) |
| HU (1) | HU184750B (ro) |
| IE (1) | IE49775B1 (ro) |
| IL (1) | IL59912A (ro) |
| IT (1) | IT1141935B (ro) |
| LU (1) | LU82411A1 (ro) |
| MY (1) | MY8500601A (ro) |
| NZ (1) | NZ193528A (ro) |
| PH (1) | PH15596A (ro) |
| PL (1) | PL125579B1 (ro) |
| PT (1) | PT71140A (ro) |
| RO (1) | RO79684A (ro) |
| SU (1) | SU860705A3 (ro) |
| ZA (1) | ZA802475B (ro) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS597193A (ja) * | 1982-07-02 | 1984-01-14 | Shionogi & Co Ltd | マロニルメチル基の異性化方法 |
| EP1673272B1 (de) * | 2003-10-08 | 2010-06-30 | Behr GmbH & Co. KG | Verfahren und vorrichtung zur herstellung eines bauteils, insbesondere eines hybridbaudteils für einen quertr ger eines fahrzeugs sowie bauteil und verwendung eines bauteils |
| JP2007508175A (ja) * | 2003-10-08 | 2007-04-05 | ベール ゲーエムベーハー ウント コー カーゲー | 構成部品、特に車両用ハイブリッド支持体と、この種の構成部品を形成する方法と、この種の構成部品の使用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1085392A (en) * | 1976-03-25 | 1980-09-09 | Masayuki Narisada | Arylmalonamido-1-oxadethiacephalosporins |
| SE443143B (sv) * | 1976-03-25 | 1986-02-17 | Shionogi & Co | Forfarande for framstellning av arylmalonamido-1-oxadetiacefalosporiner |
| US4148997A (en) * | 1977-11-07 | 1979-04-10 | Yeda Research And Development Co., Ltd. | 7-[Sulfomethyl)phenyl]acetamidocephalosporin derivatives |
| US4124762A (en) * | 1977-11-07 | 1978-11-07 | Yeda Research And Development Co., Ltd. | 7-[(Pyridylthiomethyl)phenyl]acetamido-cephalosporin derivatives |
| US4125715A (en) * | 1977-11-25 | 1978-11-14 | Yeda Research And Development Co. Ltd. | 7-[(Substituted-isothioureamethyl)phenyl]-acetamidocephalosporin derivatives |
-
1979
- 1979-05-01 US US06/035,037 patent/US4252953A/en not_active Expired - Lifetime
-
1980
- 1980-04-21 PH PH23927A patent/PH15596A/en unknown
- 1980-04-24 NZ NZ193528A patent/NZ193528A/xx unknown
- 1980-04-24 PT PT71140A patent/PT71140A/pt unknown
- 1980-04-24 AT AT0220980A patent/AT370108B/de not_active IP Right Cessation
- 1980-04-24 IL IL59912A patent/IL59912A/xx not_active IP Right Cessation
- 1980-04-24 ZA ZA00802475A patent/ZA802475B/xx unknown
- 1980-04-24 FR FR8009241A patent/FR2455605A1/fr active Granted
- 1980-04-24 CA CA000350600A patent/CA1138867A/en not_active Expired
- 1980-04-25 FI FI801345A patent/FI801345A7/fi not_active Application Discontinuation
- 1980-04-25 PL PL1980223753A patent/PL125579B1/pl unknown
- 1980-04-25 BE BE1/9799A patent/BE882980A/fr not_active IP Right Cessation
- 1980-04-25 HU HU801040A patent/HU184750B/hu not_active IP Right Cessation
- 1980-04-25 JP JP5611080A patent/JPS55153788A/ja active Granted
- 1980-04-25 DK DK177980A patent/DK177980A/da not_active Application Discontinuation
- 1980-04-26 RO RO80100971A patent/RO79684A/ro unknown
- 1980-04-28 GB GB8013972A patent/GB2047707B/en not_active Expired
- 1980-04-28 DE DE8080301392T patent/DE3061751D1/de not_active Expired
- 1980-04-28 EP EP80301392A patent/EP0018811B1/en not_active Expired
- 1980-04-29 GR GR61808A patent/GR68202B/el unknown
- 1980-04-29 LU LU82411A patent/LU82411A1/fr unknown
- 1980-04-29 IT IT21697/80A patent/IT1141935B/it active
- 1980-04-29 SU SU802913905A patent/SU860705A3/ru active
- 1980-04-29 AR AR280840A patent/AR230450A1/es active
- 1980-04-30 AU AU57914/80A patent/AU538283B2/en not_active Ceased
- 1980-04-30 BG BG047588A patent/BG34905A3/xx unknown
- 1980-04-30 EG EG268/80A patent/EG14719A/xx active
- 1980-04-30 IE IE882/80A patent/IE49775B1/en not_active IP Right Cessation
- 1980-04-30 CS CS803045A patent/CS226013B2/cs unknown
- 1980-04-30 CH CH335480A patent/CH646434A5/fr not_active IP Right Cessation
- 1980-04-30 ES ES491085A patent/ES8105316A1/es not_active Expired
- 1980-04-30 DD DD80220809A patent/DD150352A5/de unknown
- 1980-05-01 KR KR1019800001756A patent/KR840000078B1/ko not_active Expired
-
1985
- 1985-12-30 MY MY601/85A patent/MY8500601A/xx unknown
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